(1RS,4SR,5RS)-4-(5-Hydroxy-4,8-dimethyl-7-nonen-1-yl)-4-methyl-3,8-dioxabicyclooctane-1-acetic Acid from Geraniol

Article abstract of DOI:10.1021/jo00188a017

(E)-Geraniol (4) has been converted via 13 steps involving epoxidations, hydrolytic epoxide ring opening, and two ring closures to the key intermediate 3,8-dioxabicyclo<3.2.1>octane alcohol 10 having stereochemical integrity at all three centers of asymmetry.Extension of the three-carbon side chain of 10 and attachment of the acetic acid side chain at C-1 in nine steps completed the geraniol-based total synthesis of the zoapatanol related bicyclic acid 3.The total synthesis of 3 from the ketal-ketone 5 has also been described.